DE102006025777A1 - Neue Materialien für organische Elektrolumineszenzvorrichtungen - Google Patents
Neue Materialien für organische Elektrolumineszenzvorrichtungen Download PDFInfo
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- DE102006025777A1 DE102006025777A1 DE102006025777A DE102006025777A DE102006025777A1 DE 102006025777 A1 DE102006025777 A1 DE 102006025777A1 DE 102006025777 A DE102006025777 A DE 102006025777A DE 102006025777 A DE102006025777 A DE 102006025777A DE 102006025777 A1 DE102006025777 A1 DE 102006025777A1
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- BDBIKJIAGMFNPJ-UHFFFAOYSA-N (2',7'-dibromo-9,9'-spirobi[fluorene]-2-yl)-(9,9'-spirobi[fluorene]-2-yl)methanone Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(C1=C2)C3=CC=CC=C3C1=CC=C2C(=O)C(C=C12)=CC=C2C2=CC=CC=C2C11C2=CC(Br)=CC=C2C2=CC=C(Br)C=C21 BDBIKJIAGMFNPJ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Priority Applications (9)
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DE102006025777A DE102006025777A1 (de) | 2006-05-31 | 2006-05-31 | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
PCT/EP2007/004499 WO2007137725A1 (de) | 2006-05-31 | 2007-05-21 | Neue materialien für organische elektrolumineszenzvorrichtungen |
CN200780020268XA CN101460588B (zh) | 2006-05-31 | 2007-05-21 | 用于有机电致发光器件的材料 |
EP07725406.8A EP2024465B1 (de) | 2006-05-31 | 2007-05-21 | Neue materialien für organische elektrolumineszenzvorrichtungen |
JP2009512456A JP2009538841A (ja) | 2006-05-31 | 2007-05-21 | 有機エレクトロルミネセンス素子のための新規な材料 |
US12/302,560 US9206351B2 (en) | 2006-05-31 | 2007-05-21 | Materials for organic electroluminescent devices |
KR1020087032174A KR101485190B1 (ko) | 2006-05-31 | 2007-05-21 | 유기 전계발광 소자용 신규 물질 |
TW096118993A TW200813187A (en) | 2006-05-31 | 2007-05-28 | Novel materials for organic electroluminescent devices |
JP2014218439A JP2015091801A (ja) | 2006-05-31 | 2014-10-27 | 有機エレクトロルミネセンス素子のための新規な材料 |
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DE102006025777A DE102006025777A1 (de) | 2006-05-31 | 2006-05-31 | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
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US (1) | US9206351B2 (ko) |
EP (1) | EP2024465B1 (ko) |
JP (2) | JP2009538841A (ko) |
KR (1) | KR101485190B1 (ko) |
CN (1) | CN101460588B (ko) |
DE (1) | DE102006025777A1 (ko) |
TW (1) | TW200813187A (ko) |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010069444A1 (de) * | 2008-12-17 | 2010-06-24 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung |
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EP2403029A1 (en) * | 2009-02-27 | 2012-01-04 | Nippon Steel Chemical Co., Ltd. | Organic electroluminescent element |
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Families Citing this family (450)
Publication number | Priority date | Publication date | Assignee | Title |
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US9118020B2 (en) * | 2006-04-27 | 2015-08-25 | Global Oled Technology Llc | Electroluminescent devices including organic eil layer |
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JP5882318B2 (ja) | 2010-07-26 | 2016-03-09 | メルク パテント ゲーエムベーハー | デバイスにおけるナノ結晶 |
WO2012013272A1 (en) | 2010-07-26 | 2012-02-02 | Merck Patent Gmbh | Quantum dots and hosts |
DE102010033548A1 (de) | 2010-08-05 | 2012-02-09 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102010045405A1 (de) * | 2010-09-15 | 2012-03-15 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010046412B4 (de) | 2010-09-23 | 2022-01-13 | Merck Patent Gmbh | Metall-Ligand Koordinationsverbindungen |
DE102010046512A1 (de) | 2010-09-24 | 2012-03-29 | Merck Patent Gmbh | Phosphorhaltige Metallkomplexe |
DE102010048074A1 (de) | 2010-10-09 | 2012-04-12 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102010048498A1 (de) * | 2010-10-14 | 2012-04-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010048607A1 (de) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
DE102010048608A1 (de) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE112011103904B4 (de) | 2010-11-24 | 2022-12-15 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010054316A1 (de) | 2010-12-13 | 2012-06-14 | Merck Patent Gmbh | Substituierte Tetraarylbenzole |
DE102010054525A1 (de) | 2010-12-15 | 2012-04-26 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102011106849A1 (de) | 2010-12-15 | 2012-06-21 | Merck Patent Gmbh | Verfahren zur Synthese N-N verknüpfter und um die N-N Bindung rotationsgehinderter bis-N-heterocyclische Carbene und deren Einsatz als Liganden für Metallkomplexe |
DE102010055902A1 (de) | 2010-12-23 | 2012-06-28 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102010055901A1 (de) | 2010-12-23 | 2012-06-28 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
JP6022478B2 (ja) | 2011-01-13 | 2016-11-09 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
DE102012000064A1 (de) | 2011-01-21 | 2012-07-26 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
US8751777B2 (en) | 2011-01-28 | 2014-06-10 | Honeywell International Inc. | Methods and reconfigurable systems to optimize the performance of a condition based health maintenance system |
DE102011010841A1 (de) | 2011-02-10 | 2012-08-16 | Merck Patent Gmbh | (1,3)-Dioxan-5-on-Verbindungen |
DE102011011104A1 (de) | 2011-02-12 | 2012-08-16 | Merck Patent Gmbh | Substituierte Dibenzonaphtacene |
WO2012110178A1 (en) | 2011-02-14 | 2012-08-23 | Merck Patent Gmbh | Device and method for treatment of cells and cell tissue |
DE102011011539A1 (de) | 2011-02-17 | 2012-08-23 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
CN102653546B (zh) * | 2011-03-01 | 2015-10-28 | 海洋王照明科技股份有限公司 | 双极性蓝光主体材料及其制备方法与有机电致发光器件 |
CN102653677B (zh) * | 2011-03-01 | 2015-07-08 | 海洋王照明科技股份有限公司 | 双极性蓝光主体材料及其制备方法与有机电致发光器件 |
WO2012126566A1 (en) | 2011-03-24 | 2012-09-27 | Merck Patent Gmbh | Organic ionic functional materials |
CN102719236B (zh) * | 2011-03-29 | 2015-07-08 | 海洋王照明科技股份有限公司 | 双极性蓝光主体材料及其制备方法与有机电致发光器件 |
EP2694523B1 (de) | 2011-04-04 | 2017-01-11 | Merck Patent GmbH | Metallkomplexe |
JP6038879B2 (ja) | 2011-04-05 | 2016-12-07 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセント素子 |
JP6271417B2 (ja) | 2011-04-13 | 2018-01-31 | メルク パテント ゲーエムベーハー | 電子素子のための材料 |
KR102013465B1 (ko) | 2011-04-13 | 2019-08-22 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
CN103502388B (zh) | 2011-04-18 | 2016-06-01 | 默克专利有限公司 | 用于电子器件的化合物 |
WO2012143080A2 (de) | 2011-04-18 | 2012-10-26 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2012149992A1 (de) | 2011-05-04 | 2012-11-08 | Merck Patent Gmbh | Vorrichtung zur aufbewahrung von frischwaren |
EP2705550B1 (de) | 2011-05-05 | 2017-07-05 | Merck Patent GmbH | Verbindungen für elektronische vorrichtungen |
KR101884496B1 (ko) | 2011-05-05 | 2018-08-01 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
US9496502B2 (en) | 2011-05-12 | 2016-11-15 | Merck Patent Gmbh | Organic ionic compounds, compositions and electronic devices |
DE102012007810A1 (de) | 2011-05-16 | 2012-11-22 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102011102586A1 (de) | 2011-05-27 | 2012-11-29 | Merck Patent Gmbh | Organische elektronische Vorrichtung |
US9118022B2 (en) | 2011-06-03 | 2015-08-25 | Merck Patent Gmbh | Organic electroluminescent device |
US10103340B2 (en) | 2011-06-03 | 2018-10-16 | Merck Patent Gmbh | Metal complexes |
WO2013000531A1 (de) | 2011-06-28 | 2013-01-03 | Merck Patent Gmbh | Metallkomplexe |
US10454038B2 (en) | 2011-07-15 | 2019-10-22 | Kyulux, Inc. | Delayed-fluorescence material and organic electroluminescence element using same |
WO2013011956A1 (ja) * | 2011-07-15 | 2013-01-24 | 国立大学法人九州大学 | 有機エレクトロルミネッセンス素子およびそれに用いる化合物 |
KR102197165B1 (ko) | 2011-07-29 | 2021-01-04 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
KR101983019B1 (ko) | 2011-08-03 | 2019-05-28 | 메르크 파텐트 게엠베하 | 전자 소자용 물질 |
CN102924514A (zh) * | 2011-08-09 | 2013-02-13 | 海洋王照明科技股份有限公司 | 含三苯胺有机半导体材料、其制备方法和应用 |
CN102924522B (zh) * | 2011-08-09 | 2015-12-16 | 海洋王照明科技股份有限公司 | 含三苯胺有机半导体材料、其制备方法和应用 |
CN102924513A (zh) * | 2011-08-09 | 2013-02-13 | 海洋王照明科技股份有限公司 | 含三苯胺有机半导体材料、其制备方法和应用 |
CN103732602B (zh) | 2011-08-10 | 2017-02-08 | 默克专利有限公司 | 金属络合物 |
DE102012016192A1 (de) | 2011-08-19 | 2013-02-21 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
JP6203720B2 (ja) | 2011-08-22 | 2017-09-27 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子 |
BR112014006697A2 (pt) | 2011-09-21 | 2017-03-28 | Merck Patent Gmbh | derivados de carbazol para dispositivos eletroluminescentes orgânicos |
JP6182144B2 (ja) * | 2011-09-28 | 2017-08-16 | 住友化学株式会社 | 発光素子用のスピロビフルオレン化合物 |
DE102011116165A1 (de) | 2011-10-14 | 2013-04-18 | Merck Patent Gmbh | Benzodioxepin-3-on-Verbindungen |
JP6165746B2 (ja) | 2011-10-20 | 2017-07-19 | メルク パテント ゲーエムベーハー | 有機エレクトロルミッセンス素子のための材料 |
EP2782975B1 (en) | 2011-10-27 | 2018-01-10 | Merck Patent GmbH | Materials for electronic devices |
DE102011117422A1 (de) | 2011-10-28 | 2013-05-02 | Merck Patent Gmbh | Hyperverzweigte Polymere, Verfahren zu deren Herstellung sowie deren Verwendung in elektronischen Vorrichtungen |
KR102021162B1 (ko) | 2011-11-01 | 2019-09-11 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자 |
KR102310368B1 (ko) | 2011-11-17 | 2021-10-07 | 메르크 파텐트 게엠베하 | 스피로디히드로아크리딘 유도체 및 이의 유기 전계발광 소자용 재료로서의 용도 |
KR101921896B1 (ko) | 2011-12-12 | 2018-11-26 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
DE102012022880A1 (de) | 2011-12-22 | 2013-06-27 | Merck Patent Gmbh | Elektronische Vorrichtungen enthaltend organische Schichten |
KR20140117440A (ko) | 2011-12-27 | 2014-10-07 | 메르크 파텐트 게엠베하 | 1,2,3-트리아졸을 포함하는 금속 착물 |
CN106986858B (zh) | 2012-01-16 | 2019-08-27 | 默克专利有限公司 | 有机金属络合物 |
WO2013113349A1 (en) | 2012-01-30 | 2013-08-08 | Merck Patent Gmbh | Nanocrystals on fibers |
EP2814906B1 (en) | 2012-02-14 | 2016-10-19 | Merck Patent GmbH | Spirobifluorene compounds for organic electroluminescent devices |
KR102268695B1 (ko) | 2012-03-15 | 2021-06-23 | 메르크 파텐트 게엠베하 | 전자 소자 |
EP2828266B1 (de) | 2012-03-23 | 2017-10-18 | Merck Patent GmbH | 9,9'-spirobixanthenderivate für elektrolumineszenzvorrichtungen |
WO2013174471A1 (en) | 2012-05-24 | 2013-11-28 | Merck Patent Gmbh | Metal complexes comprising condensed heteroaromatic rings |
CN103450260B (zh) * | 2012-05-28 | 2017-05-17 | 海洋王照明科技股份有限公司 | 一种有机半导体材料、制备方法和电致发光器件 |
CN103450259A (zh) * | 2012-05-28 | 2013-12-18 | 海洋王照明科技股份有限公司 | 一种有机半导体材料、制备方法和电致发光器件 |
DE102012011335A1 (de) | 2012-06-06 | 2013-12-12 | Merck Patent Gmbh | Verbindungen für Organische Elekronische Vorrichtungen |
CN104471020B (zh) | 2012-07-10 | 2017-03-08 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
JP2015529637A (ja) | 2012-07-13 | 2015-10-08 | メルク パテント ゲーエムベーハー | 金属錯体 |
KR102284234B1 (ko) | 2012-07-23 | 2021-07-30 | 메르크 파텐트 게엠베하 | 2-디아릴아미노플루오렌의 유도체 및 이를 함유하는 유기 전자 화합물 |
KR102125199B1 (ko) | 2012-07-23 | 2020-06-22 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 재료 |
CN104603111A (zh) | 2012-07-23 | 2015-05-06 | 默克专利有限公司 | 芴和含有所述芴的电子器件 |
US9595681B2 (en) | 2012-07-23 | 2017-03-14 | Merck Patent Gmbh | Compounds and organic electroluminescent devices |
EP3424936B1 (de) | 2012-08-07 | 2021-04-07 | Merck Patent GmbH | Metallkomplexe |
KR102265997B1 (ko) | 2012-08-10 | 2021-06-16 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 물질 |
US10454040B2 (en) | 2012-09-18 | 2019-10-22 | Merck Patent Gmbh | Materials for electronic devices |
DE112013004610A5 (de) | 2012-09-20 | 2015-06-03 | Merck Patent Gmbh | Metallkomplexe |
EP2906661B1 (de) | 2012-10-11 | 2016-10-26 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
DE102012020167A1 (de) | 2012-10-13 | 2014-04-17 | Eberhard Karls Universität Tübingen | Metallkomplexe |
US9595682B2 (en) | 2012-10-30 | 2017-03-14 | Massachusetts Institute Of Technology | Organic conductive materials and devices |
EP2915199B1 (de) | 2012-10-31 | 2021-03-31 | Merck Patent GmbH | Elektronische vorrichtung |
DE102012021650A1 (de) | 2012-11-03 | 2014-05-08 | Eberhard Karls Universität Tübingen | Metallkomplexe |
CN104781247B (zh) | 2012-11-12 | 2017-08-15 | 默克专利有限公司 | 用于电子器件的材料 |
JP6407877B2 (ja) | 2012-11-20 | 2018-10-17 | メルク パテント ゲーエムベーハー | 電子素子の製造のための高純度溶媒における調合物 |
EP2926385B1 (de) | 2012-11-30 | 2020-08-05 | Merck Patent GmbH | Elektronische vorrichtung |
CN103509053A (zh) * | 2012-12-10 | 2014-01-15 | Tcl集团股份有限公司 | 蓝色磷光双极性化合物、制备方法和应用及电致发光器件 |
US20150329772A1 (en) | 2013-01-03 | 2015-11-19 | Merck Patent Gmbh | Materials for Electronic Devices |
WO2014106524A2 (de) | 2013-01-03 | 2014-07-10 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
DE102013008189A1 (de) | 2013-05-14 | 2014-12-04 | Eberhard Karls Universität Tübingen | Metallkomplexe |
JP2016525781A (ja) | 2013-07-29 | 2016-08-25 | メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングMerck Patent GmbH | 電気光学素子およびその使用 |
WO2015014434A1 (de) | 2013-07-30 | 2015-02-05 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
EP3027708B1 (de) | 2013-07-30 | 2020-05-13 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
CN103435529A (zh) * | 2013-07-31 | 2013-12-11 | 西南科技大学 | N取代双吲哚化合物及其制备方法 |
EP3052505B1 (de) | 2013-10-02 | 2021-06-23 | Merck Patent GmbH | Borenthaltende verbindungen |
EP3077475B1 (en) | 2013-12-06 | 2018-07-04 | Merck Patent GmbH | Compositions containing a polymeric binder which comprises acrylic and/or methacrylic acid ester units |
KR102380808B1 (ko) | 2013-12-06 | 2022-03-30 | 메르크 파텐트 게엠베하 | 치환 옥세핀 |
KR101772371B1 (ko) | 2013-12-06 | 2017-08-29 | 메르크 파텐트 게엠베하 | 화합물 및 유기 전자 소자 |
KR101993129B1 (ko) | 2013-12-12 | 2019-06-26 | 메르크 파텐트 게엠베하 | 전자 소자용 물질 |
CN105829292A (zh) | 2013-12-19 | 2016-08-03 | 默克专利有限公司 | 杂环螺环化合物 |
EP2927221A1 (en) | 2014-03-31 | 2015-10-07 | Commonwealth Scientific and Industrial Research Organisation | Diamine compounds for phosphorescent diazaborole metal complexes and electroluminescent devices |
US9768397B2 (en) | 2014-03-31 | 2017-09-19 | Commonwealth Scientific And Industrial Research Organisation | Phenylenediamine compounds for phosphorescent diazaborole metal complexes |
CN103922915B (zh) * | 2014-04-14 | 2016-05-11 | 国家纳米科学中心 | 一种具有压致变色性质的双芘类化合物、制备方法及其应用 |
EP3137458B1 (de) | 2014-04-30 | 2019-04-24 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
WO2015169412A1 (de) | 2014-05-05 | 2015-11-12 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
DE102015006708A1 (de) | 2014-06-12 | 2015-12-17 | Merck Patent Gmbh | Metallkomplexe |
JP6556764B2 (ja) | 2014-06-25 | 2019-08-07 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
EP2960315A1 (de) | 2014-06-27 | 2015-12-30 | cynora GmbH | Organische Elektrolumineszenzvorrichtung |
EP2963044A1 (de) | 2014-06-30 | 2016-01-06 | cynora GmbH | Zweikernige Metall(I)-Komplexe mit tetradentaten Liganden für optoelektronische Anwendungen |
KR102479149B1 (ko) | 2014-07-21 | 2022-12-19 | 메르크 파텐트 게엠베하 | 전자 소자용 재료 |
DE102014012818A1 (de) | 2014-08-28 | 2016-03-03 | Eberhard Karls Universität Tübingen | Metallkomplexe |
WO2016034262A1 (de) | 2014-09-05 | 2016-03-10 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
EP3204463B1 (de) | 2014-10-08 | 2019-04-17 | cynora GmbH | Metall-komplexe mit tridentaten liganden für optoelektronische anwendungen |
JP2017537085A (ja) | 2014-11-11 | 2017-12-14 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
WO2016079097A1 (de) | 2014-11-18 | 2016-05-26 | Cynora Gmbh | Kupfer(i)komplexe für optoelektronische anwendungen |
CN115838341A (zh) | 2014-12-12 | 2023-03-24 | 默克专利有限公司 | 具有可溶性基团的有机化合物 |
EP3241248A1 (de) | 2014-12-30 | 2017-11-08 | Merck Patent GmbH | Formulierungen und elektronische vorrichtungen |
WO2016119992A1 (en) | 2015-01-30 | 2016-08-04 | Merck Patent Gmbh | Materials for electronic devices |
CN107532013A (zh) | 2015-01-30 | 2018-01-02 | 默克专利有限公司 | 具有低粒子含量的制剂 |
EP3254317B1 (de) | 2015-02-03 | 2019-07-31 | Merck Patent GmbH | Metallkomplexe |
US10651382B2 (en) | 2015-03-30 | 2020-05-12 | Merck Patent Gmbh | Formulation of an organic functional material comprising a siloxane solvent |
EP3307735A1 (en) | 2015-06-10 | 2018-04-18 | Merck Patent GmbH | Materials for organic electroluminescent devices |
US10808170B2 (en) | 2015-06-12 | 2020-10-20 | Merck Patent Gmbh | Esters containing non-aromatic cycles as solvents for OLED formulations |
CN107836046B (zh) | 2015-07-15 | 2020-08-04 | 默克专利有限公司 | 包含有机半导体化合物的组合物 |
CN114805091A (zh) | 2015-07-22 | 2022-07-29 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
GB201513037D0 (en) | 2015-07-23 | 2015-09-09 | Merck Patent Gmbh | Phenyl-derived compound for use in organic electronic devices |
EP3328825B1 (en) | 2015-07-29 | 2023-06-28 | Merck Patent GmbH | Materials for organic electroluminescent devices |
KR20180031766A (ko) | 2015-07-30 | 2018-03-28 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 재료 |
CN107922335B (zh) | 2015-08-13 | 2021-06-04 | 默克专利有限公司 | 六甲基二氢化茚 |
KR102599157B1 (ko) | 2015-08-14 | 2023-11-06 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 페녹사진 유도체 |
EP3341981B1 (en) | 2015-08-28 | 2020-08-19 | Merck Patent GmbH | Formulation of an organic functional material comprising an epoxy group containing solvent |
WO2017036573A1 (en) | 2015-08-28 | 2017-03-09 | Merck Patent Gmbh | Compounds for electronic devices |
DE102015013381A1 (de) | 2015-10-14 | 2017-04-20 | Eberhard Karls Universität Tübingen | Metallkomplexe |
US11355714B2 (en) | 2015-10-27 | 2022-06-07 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
CN108368361A (zh) | 2015-12-10 | 2018-08-03 | 默克专利有限公司 | 含有包含非芳族环的酮的制剂 |
DE102015016016A1 (de) | 2015-12-10 | 2017-06-14 | Eberhard Karls Universität Tübingen | Metallkomplexe |
JP7051684B2 (ja) | 2015-12-15 | 2022-04-11 | メルク パテント ゲーエムベーハー | 有機電子調合物のための溶媒として芳香族基を含むエステル |
KR20180095028A (ko) | 2015-12-16 | 2018-08-24 | 메르크 파텐트 게엠베하 | 둘 이상의 상이한 용매의 혼합물을 함유하는 제형 |
WO2017102052A1 (en) | 2015-12-16 | 2017-06-22 | Merck Patent Gmbh | Formulations containing a solid solvent |
CN108603107B (zh) | 2016-02-05 | 2022-08-26 | 默克专利有限公司 | 用于电子器件的材料 |
US10840448B2 (en) | 2016-02-17 | 2020-11-17 | Merck Patent Gmbh | Formulation of an organic functional material |
EP3423542B1 (de) | 2016-03-03 | 2020-07-22 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
DE102016003104A1 (de) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Behälter umfassend eine Formulierung enthaltend mindestens einen organischen Halbleiter |
TWI745361B (zh) | 2016-03-17 | 2021-11-11 | 德商麥克專利有限公司 | 具有螺聯茀結構之化合物 |
EP3442968A1 (de) | 2016-04-11 | 2019-02-20 | Merck Patent GmbH | Heterocyclische verbindungen mit dibenzofuran- und/oder dibenzothiophen-strukturen |
JP7046831B2 (ja) | 2016-04-29 | 2022-04-04 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンスデバイス用の材料 |
CN116283863A (zh) | 2016-06-03 | 2023-06-23 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
WO2017216129A1 (en) | 2016-06-16 | 2017-12-21 | Merck Patent Gmbh | Formulation of an organic functional material |
CN109312183A (zh) | 2016-06-17 | 2019-02-05 | 默克专利有限公司 | 有机功能材料的制剂 |
TW201815998A (zh) | 2016-06-28 | 2018-05-01 | 德商麥克專利有限公司 | 有機功能材料之調配物 |
WO2018001990A1 (de) | 2016-06-30 | 2018-01-04 | Merck Patent Gmbh | Verfahren zur auftrennung von enantiomerenmischungen von metallkomplexen |
TWI745395B (zh) | 2016-07-08 | 2021-11-11 | 德商麥克專利有限公司 | 有機電致發光裝置用之材料 |
TWI749026B (zh) | 2016-07-14 | 2021-12-11 | 德商麥克專利有限公司 | 金屬錯合物 |
WO2018019688A1 (de) | 2016-07-25 | 2018-02-01 | Merck Patent Gmbh | Metallkomplexe für den einsatz als emitter in organischen elektrolumineszenzvorrichtungen |
TW201817738A (zh) | 2016-07-25 | 2018-05-16 | 德商麥克專利有限公司 | 金屬錯合物 |
WO2018024719A1 (en) | 2016-08-04 | 2018-02-08 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018041769A1 (de) | 2016-08-30 | 2018-03-08 | Merck Patent Gmbh | Bl- und trinukleare metallkomplexe aufgebaut aus zwei miteinander verknüpften tripodalen hexadentaten liganden zur verwendung in elektrolumineszenzvorrichtungen |
JP2019530676A (ja) | 2016-09-14 | 2019-10-24 | メルク パテント ゲーエムベーハー | カルバゾール構造を有する化合物 |
EP3512841B1 (de) | 2016-09-14 | 2023-04-26 | Merck Patent GmbH | Verbindungen mit spirobifluoren-strukturen |
WO2018054798A1 (de) | 2016-09-21 | 2018-03-29 | Merck Patent Gmbh | Binukleare metallkomplexe für den einsatz als emitter in organischen elektrolumineszenzvorrichtungen |
TWI766884B (zh) | 2016-09-30 | 2022-06-11 | 德商麥克專利有限公司 | 具有二氮雜二苯并呋喃或二氮雜二苯并噻吩結構的化合物、其製法及其用途 |
CN109790173B (zh) | 2016-09-30 | 2022-09-06 | 默克专利有限公司 | 具有二氮杂二苯并呋喃或二氮杂二苯并噻吩结构的咔唑 |
TWI764942B (zh) | 2016-10-10 | 2022-05-21 | 德商麥克專利有限公司 | 電子裝置 |
WO2018069196A1 (de) | 2016-10-12 | 2018-04-19 | Merck Patent Gmbh | Binukleare metallkomplexe sowie elektronische vorrichtungen, insbesondere organische elektrolumineszenzvorrichtungen, enthaltend diese metallkomplexe |
WO2018069197A1 (de) | 2016-10-12 | 2018-04-19 | Merck Patent Gmbh | Metallkomplexe |
KR102472249B1 (ko) | 2016-10-13 | 2022-11-29 | 메르크 파텐트 게엠베하 | 금속 착물 |
DE102017008794A1 (de) | 2016-10-17 | 2018-04-19 | Merck Patent Gmbh | Materialien zur Verwendung in elektronischen Vorrichtungen |
WO2018077769A1 (de) | 2016-10-25 | 2018-05-03 | Merck Patent Gmbh | Metallkomplexe |
JP7013459B2 (ja) | 2016-10-31 | 2022-01-31 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
EP3532565B1 (en) | 2016-10-31 | 2021-04-21 | Merck Patent GmbH | Formulation of an organic functional material |
WO2018083053A1 (de) | 2016-11-02 | 2018-05-11 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
KR20230121632A (ko) | 2016-11-08 | 2023-08-18 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
EP3538521A1 (de) | 2016-11-09 | 2019-09-18 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
TWI756292B (zh) | 2016-11-14 | 2022-03-01 | 德商麥克專利有限公司 | 具有受體基團與供體基團之化合物 |
US20190352318A1 (en) | 2016-11-17 | 2019-11-21 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
TW201833118A (zh) | 2016-11-22 | 2018-09-16 | 德商麥克專利有限公司 | 用於電子裝置之材料 |
US11713319B2 (en) | 2016-11-30 | 2023-08-01 | Merck Patent Gmbh | Compounds having valerolactam structures |
EP3548485B1 (de) | 2016-12-05 | 2021-01-20 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
EP3548486B1 (de) | 2016-12-05 | 2021-10-27 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
TW201831468A (zh) | 2016-12-05 | 2018-09-01 | 德商麥克專利有限公司 | 含氮的雜環化合物 |
US10892414B2 (en) | 2016-12-06 | 2021-01-12 | Merck Patent Gmbh | Process for making electronic device |
JP7091337B2 (ja) | 2016-12-13 | 2022-06-27 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
WO2018114744A1 (en) | 2016-12-20 | 2018-06-28 | Merck Patent Gmbh | A white light emitting solid state light source |
JP7114596B2 (ja) | 2016-12-22 | 2022-08-08 | メルク パテント ゲーエムベーハー | 少なくとも2種の有機機能性化合物を含む混合物 |
CN109996828A (zh) | 2016-12-22 | 2019-07-09 | 默克专利有限公司 | 用于电子器件的材料 |
WO2018125512A1 (en) | 2016-12-27 | 2018-07-05 | Dow Global Technologies Llc | High triplet energy phosphine oxide compounds for oled application |
EP3565816B1 (de) | 2017-01-04 | 2022-03-16 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
US10964894B2 (en) | 2017-01-25 | 2021-03-30 | Merck Patent Gmbh | Carbazole derivatives |
TWI763772B (zh) | 2017-01-30 | 2022-05-11 | 德商麥克專利有限公司 | 電子裝置之有機元件的形成方法 |
TWI791481B (zh) | 2017-01-30 | 2023-02-11 | 德商麥克專利有限公司 | 形成有機電致發光(el)元件之方法 |
EP3573985B1 (de) | 2017-01-30 | 2023-01-18 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
KR102683465B1 (ko) | 2017-02-02 | 2024-07-09 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
TW201835075A (zh) | 2017-02-14 | 2018-10-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
KR20180097807A (ko) | 2017-02-23 | 2018-09-03 | 삼성디스플레이 주식회사 | 다환 화합물 및 이를 포함한 유기 발광 소자 |
EP3590141A1 (en) | 2017-03-01 | 2020-01-08 | Merck Patent GmbH | Organic electroluminescent device |
WO2018157981A1 (de) | 2017-03-02 | 2018-09-07 | Merck Patent Gmbh | Materialien für organische elektronische vorrichtungen |
TW201843143A (zh) | 2017-03-13 | 2018-12-16 | 德商麥克專利有限公司 | 含有芳基胺結構之化合物 |
EP3596066B1 (de) | 2017-03-15 | 2022-05-18 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
TWI780134B (zh) | 2017-03-29 | 2022-10-11 | 德商麥克專利有限公司 | 芳族化合物 |
CN110446611B (zh) | 2017-03-31 | 2021-05-25 | 默克专利有限公司 | 用于有机发光二极管(oled)的印刷方法 |
JP7200128B2 (ja) | 2017-04-10 | 2023-01-06 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
WO2018189134A1 (de) | 2017-04-13 | 2018-10-18 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
KR102585423B1 (ko) | 2017-04-25 | 2023-10-05 | 메르크 파텐트 게엠베하 | 전자 디바이스용 화합물 |
CN110546236A (zh) | 2017-05-03 | 2019-12-06 | 默克专利有限公司 | 有机功能材料的制剂 |
EP3621971B1 (en) | 2017-05-11 | 2021-06-23 | Merck Patent GmbH | Carbazole-based bodipys for organic electroluminescent devices |
EP3621970B1 (en) | 2017-05-11 | 2021-01-13 | Merck Patent GmbH | Organoboron complexes for organic electroluminescent devices |
JP2020520970A (ja) | 2017-05-22 | 2020-07-16 | メルク パテント ゲーエムベーハー | 電子デバイス用六環性ヘテロ芳香族化合物 |
TW201920343A (zh) | 2017-06-21 | 2019-06-01 | 德商麥克專利有限公司 | 電子裝置用材料 |
WO2018234346A1 (en) | 2017-06-23 | 2018-12-27 | Merck Patent Gmbh | MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES |
KR20240110060A (ko) | 2017-06-26 | 2024-07-12 | 메르크 파텐트 게엠베하 | 균질 혼합물 |
KR20240059634A (ko) | 2017-06-28 | 2024-05-07 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
TWI813576B (zh) | 2017-07-03 | 2023-09-01 | 德商麥克專利有限公司 | 具有低含量苯酚類雜質的調配物 |
EP3649123B1 (de) | 2017-07-05 | 2023-03-15 | Merck Patent GmbH | Zusammensetzung für organische elektronische vorrichtungen |
JP7247121B2 (ja) | 2017-07-05 | 2023-03-28 | メルク パテント ゲーエムベーハー | 有機電子デバイスのための組成物 |
WO2019016184A1 (en) | 2017-07-18 | 2019-01-24 | Merck Patent Gmbh | FORMULATION OF AN ORGANIC FUNCTIONAL MATERIAL |
TWI776926B (zh) | 2017-07-25 | 2022-09-11 | 德商麥克專利有限公司 | 金屬錯合物 |
US20200212301A1 (en) | 2017-07-28 | 2020-07-02 | Merck Patent Gmbh | Spirobifluorene derivatives for use in electronic devices |
CN118405981A (zh) | 2017-09-08 | 2024-07-30 | 默克专利有限公司 | 用于电子器件的材料 |
CN111065640B (zh) | 2017-09-12 | 2023-04-18 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
KR102671945B1 (ko) | 2017-10-06 | 2024-06-03 | 메르크 파텐트 게엠베하 | 유기 전계발광 디바이스용 재료 |
CN108675975A (zh) | 2017-10-17 | 2018-10-19 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
US11437588B2 (en) | 2017-10-24 | 2022-09-06 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
TWI785142B (zh) | 2017-11-14 | 2022-12-01 | 德商麥克專利有限公司 | 用於有機電子裝置之組成物 |
JP2021504356A (ja) | 2017-11-23 | 2021-02-15 | メルク パテント ゲーエムベーハー | 電子デバイス用材料 |
TWI820057B (zh) | 2017-11-24 | 2023-11-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
TWI838352B (zh) | 2017-11-24 | 2024-04-11 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
CN111406062B (zh) | 2017-12-13 | 2024-01-19 | Udc爱尔兰有限公司 | 金属络合物 |
KR102666621B1 (ko) | 2017-12-15 | 2024-05-16 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
KR102638811B1 (ko) | 2017-12-15 | 2024-02-21 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 치환된 방향족 아민 |
TW201938562A (zh) | 2017-12-19 | 2019-10-01 | 德商麥克專利有限公司 | 雜環化合物 |
US20210036245A1 (en) | 2017-12-20 | 2021-02-04 | Merck Patent Gmbh | Heteroaromatic compounds |
TWI811290B (zh) | 2018-01-25 | 2023-08-11 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
CN111699192B (zh) | 2018-02-13 | 2024-03-08 | Udc爱尔兰有限公司 | 金属络合物 |
CN111712551A (zh) | 2018-02-26 | 2020-09-25 | 默克专利有限公司 | 有机功能材料的制剂 |
TWI802656B (zh) | 2018-03-06 | 2023-05-21 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
TW201938761A (zh) | 2018-03-06 | 2019-10-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
CN111819167A (zh) | 2018-03-16 | 2020-10-23 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
TWI828664B (zh) | 2018-03-19 | 2024-01-11 | 愛爾蘭商Udc愛爾蘭責任有限公司 | 金屬錯合物 |
WO2019229011A1 (de) | 2018-05-30 | 2019-12-05 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
CN112219292A (zh) | 2018-06-07 | 2021-01-12 | 默克专利有限公司 | 有机电致发光器件 |
CN112236488A (zh) | 2018-06-15 | 2021-01-15 | 默克专利有限公司 | 有机功能材料的制剂 |
US11581497B2 (en) | 2018-07-09 | 2023-02-14 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
KR20210033497A (ko) | 2018-07-20 | 2021-03-26 | 메르크 파텐트 게엠베하 | 유기 전계발광 디바이스용 재료 |
CN110857267B (zh) * | 2018-08-22 | 2022-12-09 | 昱镭光电科技股份有限公司 | 芳香酮化合物及其有机发光器件 |
TWI837167B (zh) | 2018-08-28 | 2024-04-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
TWI823993B (zh) | 2018-08-28 | 2023-12-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
EP3844243B1 (en) | 2018-08-28 | 2022-06-22 | Merck Patent GmbH | Materials for organic electroluminescent devices |
TW202030902A (zh) | 2018-09-12 | 2020-08-16 | 德商麥克專利有限公司 | 電致發光裝置 |
TWI826522B (zh) | 2018-09-12 | 2023-12-21 | 德商麥克專利有限公司 | 電致發光裝置 |
WO2020053150A1 (en) | 2018-09-12 | 2020-03-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
CN112740432B (zh) | 2018-09-24 | 2024-09-20 | 默克专利有限公司 | 用于生产粒状材料的方法 |
WO2020064662A2 (de) | 2018-09-27 | 2020-04-02 | Merck Patent Gmbh | Verfahren zur herstellung von sterisch gehinderten stickstoffhaltigen heteroaromatischen verbindungen |
KR20210068054A (ko) | 2018-09-27 | 2021-06-08 | 메르크 파텐트 게엠베하 | 유기 전자 디바이스에서 활성 화합물로 사용될 수 있는 화합물 |
WO2020089138A1 (en) | 2018-10-31 | 2020-05-07 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP3877369A1 (de) | 2018-11-05 | 2021-09-15 | Merck Patent GmbH | In einer organischen elektronischen vorrichtung einsetzbare verbindungen |
WO2020094542A1 (de) | 2018-11-06 | 2020-05-14 | Merck Patent Gmbh | 5,6-diphenyl-5,6-dihydro-dibenz[c,e][1,2]azaphosphorin- und 6-phenyl-6h-dibenzo[c,e][1,2]thiazin-5,5-dioxid-derivate und ähnliche verbindungen als organische elektrolumineszenzmaterialien für oleds |
KR20210083347A (ko) | 2018-11-06 | 2021-07-06 | 메르크 파텐트 게엠베하 | 전자 디바이스의 유기 소자의 형성 방법 |
US20220006018A1 (en) | 2018-11-14 | 2022-01-06 | Merck Patent Gmbh | Compounds that can be used for producing an organic electronic device |
WO2020099307A1 (de) | 2018-11-15 | 2020-05-22 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
TW202039493A (zh) | 2018-12-19 | 2020-11-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
EP3911655A1 (en) | 2019-01-16 | 2021-11-24 | Merck Patent GmbH | Materials for organic electroluminescent devices |
KR20210125531A (ko) | 2019-02-11 | 2021-10-18 | 메르크 파텐트 게엠베하 | 3개의 오르토-메탈레이트화 두자리 리간드 및 광학 배향 이방성을 포함하는 단핵 이리듐 착물 |
WO2020169241A1 (de) | 2019-02-18 | 2020-08-27 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
US20220127286A1 (en) | 2019-03-04 | 2022-04-28 | Merck Patent Gmbh | Ligands for nano-sized materials |
KR20210137148A (ko) | 2019-03-12 | 2021-11-17 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
US20220177478A1 (en) | 2019-03-20 | 2022-06-09 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
CN111170907B (zh) * | 2019-03-21 | 2022-04-08 | 广东聚华印刷显示技术有限公司 | 热活化延迟荧光材料及其制备方法和应用、有机电致发光器件 |
WO2020193447A1 (de) | 2019-03-25 | 2020-10-01 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
KR20210151882A (ko) | 2019-04-11 | 2021-12-14 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
US20220209141A1 (en) | 2019-04-15 | 2022-06-30 | Merck Patent Gmbh | Metal complexes |
JP2022546334A (ja) | 2019-08-26 | 2022-11-04 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセントデバイスのための材料 |
CN114341117A (zh) | 2019-09-02 | 2022-04-12 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
TW202122558A (zh) | 2019-09-03 | 2021-06-16 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
EP4031546A1 (en) | 2019-09-16 | 2022-07-27 | Merck Patent GmbH | Materials for organic electroluminescent devices |
CN114342103A (zh) | 2019-09-19 | 2022-04-12 | 默克专利有限公司 | 两种主体材料的混合物和包含所述混合物的有机电致发光器件 |
CN114401945A (zh) | 2019-09-20 | 2022-04-26 | 默克专利有限公司 | 作为用于电子器件的材料的迫位缩合杂环化合物 |
WO2021078710A1 (en) | 2019-10-22 | 2021-04-29 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2021078831A1 (de) | 2019-10-25 | 2021-04-29 | Merck Patent Gmbh | In einer organischen elektronischen vorrichtung einsetzbare verbindungen |
KR20220092590A (ko) | 2019-11-04 | 2022-07-01 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
TW202134252A (zh) | 2019-11-12 | 2021-09-16 | 德商麥克專利有限公司 | 有機電致發光裝置用材料 |
TW202136181A (zh) | 2019-12-04 | 2021-10-01 | 德商麥克專利有限公司 | 有機電致發光裝置用的材料 |
CN114787173A (zh) | 2019-12-04 | 2022-07-22 | 默克专利有限公司 | 金属络合物 |
TW202136471A (zh) | 2019-12-17 | 2021-10-01 | 德商麥克專利有限公司 | 有機電致發光裝置用的材料 |
JP2023506572A (ja) | 2019-12-18 | 2023-02-16 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 有機エレクトロルミネッセンス素子のための芳香族化合物 |
KR20220116008A (ko) | 2019-12-19 | 2022-08-19 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 다환 화합물 |
CN115052865A (zh) | 2020-01-29 | 2022-09-13 | 默克专利有限公司 | 苯并咪唑衍生物 |
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KR20220154751A (ko) | 2020-03-17 | 2022-11-22 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 복소환 화합물 |
US20230337537A1 (en) | 2020-03-23 | 2023-10-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
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EP4169082A1 (de) | 2020-06-23 | 2023-04-26 | Merck Patent GmbH | Verfahren zur herstellung einer mischung |
US20230312612A1 (en) | 2020-06-29 | 2023-10-05 | Merck Patent Gmbh | Heteroaromatic compounds for organic electroluminescent devices |
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EP4196486A1 (de) | 2020-08-13 | 2023-06-21 | Merck Patent GmbH | Metallkomplexe |
KR20230053629A (ko) | 2020-08-18 | 2023-04-21 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
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US20230416264A1 (en) | 2020-12-02 | 2023-12-28 | Merck Patent Gmbh | Heterocyclic compounds for organic electroluminescent devices |
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US20240092783A1 (en) | 2021-03-18 | 2024-03-21 | Merck Patent Gmbh | Heteroaromatic compounds for organic electroluminescent devices |
EP4079742A1 (de) | 2021-04-14 | 2022-10-26 | Merck Patent GmbH | Metallkomplexe |
JP2024515366A (ja) | 2021-04-23 | 2024-04-09 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
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WO2023094412A1 (de) | 2021-11-25 | 2023-06-01 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
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TW202411366A (zh) | 2022-06-07 | 2024-03-16 | 德商麥克專利有限公司 | 藉由組合油墨來印刷電子裝置功能層之方法 |
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WO2024126635A1 (en) | 2022-12-16 | 2024-06-20 | Merck Patent Gmbh | Formulation of an organic functional material |
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WO2024133048A1 (en) | 2022-12-20 | 2024-06-27 | Merck Patent Gmbh | Method for preparing deuterated aromatic compounds |
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WO2024153568A1 (de) | 2023-01-17 | 2024-07-25 | Merck Patent Gmbh | Heterocyclen für organische elektrolumineszenzvorrichtungen |
WO2024170605A1 (en) | 2023-02-17 | 2024-08-22 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2024184050A1 (de) | 2023-03-07 | 2024-09-12 | Merck Patent Gmbh | Cyclische stickstoffverbindungen für organische elektrolumineszenzvorrichtungen |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3164596B2 (ja) * | 1991-04-12 | 2001-05-08 | 出光興産株式会社 | ヒドロキシアリールアミン化合物とその製造法及びこれを用いた電子写真感光体 |
JPH07110940B2 (ja) * | 1991-06-05 | 1995-11-29 | 住友化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
US5378519A (en) * | 1992-04-28 | 1995-01-03 | Canon Kabushiki Kaisha | Electroluminescent device |
DE69305262T2 (de) * | 1992-07-13 | 1997-04-30 | Eastman Kodak Co | Einen inneren Übergang aufweisende organisch elektrolumineszierende Vorrichtung mit einer neuen Zusammensetzung |
DE69412567T2 (de) * | 1993-11-01 | 1999-02-04 | Hodogaya Chemical Co., Ltd., Tokio/Tokyo | Aminverbindung und sie enthaltende Elektrolumineszenzvorrichtung |
JP3503403B2 (ja) * | 1997-03-17 | 2004-03-08 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子用発光材料およびそれを使用した有機エレクトロルミネッセンス素子 |
JP4038833B2 (ja) * | 1997-05-21 | 2008-01-30 | 三菱化学株式会社 | 有機電界発光素子 |
US6458475B1 (en) * | 1999-11-24 | 2002-10-01 | The Trustee Of Princeton University | Organic light emitting diode having a blue phosphorescent molecule as an emitter |
DE60045110D1 (de) * | 1999-12-01 | 2010-11-25 | Univ Princeton | Erungsmittel in organischen led's |
JP3873707B2 (ja) * | 2001-10-26 | 2007-01-24 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子用材料およびそれを使用した有機エレクトロルミネッセンス素子 |
JP2003249372A (ja) * | 2002-02-21 | 2003-09-05 | Hayashibara Biochem Lab Inc | 有機電界発光素子 |
JP4243328B2 (ja) | 2002-03-11 | 2009-03-25 | 財団法人神奈川科学技術アカデミー | フェニルアゾメチン系カルバゾールデンドリマーと有機el素子 |
DE10317556B4 (de) * | 2003-04-15 | 2021-05-12 | Merck Patent Gmbh | Mischungen von organischen zur Emission befähigten Halbleitern und Matrixmaterialien, deren Verwendung und Elektronikbauteile enthaltend diese |
EP1717291A3 (de) | 2003-04-15 | 2007-03-21 | Merck Patent GmbH | Mischungen von organischen, zur Emission befähigten Halbleitern und Maxtrixmaterialien, deren Verwendung und diese Mischungen enthaltende Elektronikbauteile |
JP4082297B2 (ja) * | 2003-07-29 | 2008-04-30 | 三菱化学株式会社 | 有機化合物、電荷輸送材料、有機電界発光素子材料および有機電界発光素子 |
JP4438394B2 (ja) * | 2003-10-30 | 2010-03-24 | 三菱化学株式会社 | 有機金属錯体およびそれを用いた有機電界発光素子 |
JP2005158289A (ja) * | 2003-11-20 | 2005-06-16 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP4992183B2 (ja) * | 2004-02-10 | 2012-08-08 | 三菱化学株式会社 | 発光層形成材料及び有機電界発光素子 |
US7011871B2 (en) * | 2004-02-20 | 2006-03-14 | E. I. Du Pont De Nemours And Company | Charge transport compounds and electronic devices made with such compounds |
CN101087776B (zh) * | 2004-12-24 | 2012-07-04 | 先锋公司 | 有机化合物、电荷传输材料和有机电致发光元件 |
KR100713989B1 (ko) | 2005-07-15 | 2007-05-04 | 삼성에스디아이 주식회사 | 백색 유기 발광 소자 및 그의 제조방법 |
-
2006
- 2006-05-31 DE DE102006025777A patent/DE102006025777A1/de not_active Withdrawn
-
2007
- 2007-05-21 CN CN200780020268XA patent/CN101460588B/zh not_active Expired - Fee Related
- 2007-05-21 US US12/302,560 patent/US9206351B2/en not_active Expired - Fee Related
- 2007-05-21 WO PCT/EP2007/004499 patent/WO2007137725A1/de active Application Filing
- 2007-05-21 KR KR1020087032174A patent/KR101485190B1/ko active IP Right Grant
- 2007-05-21 JP JP2009512456A patent/JP2009538841A/ja not_active Withdrawn
- 2007-05-21 EP EP07725406.8A patent/EP2024465B1/de not_active Not-in-force
- 2007-05-28 TW TW096118993A patent/TW200813187A/zh unknown
-
2014
- 2014-10-27 JP JP2014218439A patent/JP2015091801A/ja active Pending
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010069444A1 (de) * | 2008-12-17 | 2010-06-24 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung |
WO2010069442A1 (de) * | 2008-12-17 | 2010-06-24 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung |
DE102008063490B4 (de) | 2008-12-17 | 2023-06-15 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung und Verfahren zum Einstellen des Farbortes einer weiß emittierenden Elektrolumineszenzvorrichtung |
EP2403029A1 (en) * | 2009-02-27 | 2012-01-04 | Nippon Steel Chemical Co., Ltd. | Organic electroluminescent element |
EP2403029A4 (en) * | 2009-02-27 | 2012-08-08 | Nippon Steel Chemical Co | ORGANIC ELECTROLUMINESCENT ELEMENT |
DE102009012346B4 (de) | 2009-03-09 | 2024-02-15 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung und Verfahren zu deren Herstellung |
US9062003B2 (en) | 2010-10-06 | 2015-06-23 | Glaxosmithkline Llc | Benzimidazole derivatives as PI3 kinase inhibitors |
US8865912B2 (en) | 2010-10-06 | 2014-10-21 | Glaxosmithkline Llc | Benzimidazole derivatives as PI3 kinase inhibitors |
US8674090B2 (en) | 2010-10-06 | 2014-03-18 | Glaxosmithkline Llc | Benzimidazole derivatives as PI3 kinase inhibitors |
US9156797B2 (en) | 2010-10-06 | 2015-10-13 | Glaxosmithkline Llc | Benzimidazole derivatives as PI3 kinase inhibitors |
US9872860B2 (en) | 2010-10-06 | 2018-01-23 | Glaxosmithkline Llc | Benzimidazole derivatives as PI3 kinase inhibitors |
US10314845B2 (en) | 2010-10-06 | 2019-06-11 | Glaxosmithkline Llc | Benzimidazole derivatives as PI3 kinase inhibitors |
US10660898B2 (en) | 2010-10-06 | 2020-05-26 | Glaxosmithkline Llc | Benzimidazole derivatives as PI3 kinase inhibitors |
US8541411B2 (en) | 2010-10-06 | 2013-09-24 | Glaxosmithkline Llc | Benzimidazole derivatives as PI3 kinase inhibitors |
US8435988B2 (en) | 2010-10-06 | 2013-05-07 | Glaxosmithkline Llc | Benzimidazole derivatives as P13 kinase inhibitors |
WO2015175680A1 (en) * | 2014-05-14 | 2015-11-19 | President And Fellows Of Harvard College | Organic light-emitting diode materials |
US9972795B2 (en) | 2014-05-14 | 2018-05-15 | Presidents And Fellows Of Harvard College | Organic light-emitting diode materials |
WO2015192941A1 (de) * | 2014-06-18 | 2015-12-23 | Merck Patent Gmbh | Zusammensetzungen für elektronische vorrichtungen |
US10847727B2 (en) | 2014-06-18 | 2020-11-24 | Merck Patent Gmbh | Compositions for electronic devices |
Also Published As
Publication number | Publication date |
---|---|
KR101485190B1 (ko) | 2015-01-22 |
KR20090029752A (ko) | 2009-03-23 |
US20090167166A1 (en) | 2009-07-02 |
US9206351B2 (en) | 2015-12-08 |
EP2024465B1 (de) | 2016-01-13 |
WO2007137725A1 (de) | 2007-12-06 |
JP2015091801A (ja) | 2015-05-14 |
CN101460588A (zh) | 2009-06-17 |
EP2024465A1 (de) | 2009-02-18 |
CN101460588B (zh) | 2013-05-08 |
JP2009538841A (ja) | 2009-11-12 |
TW200813187A (en) | 2008-03-16 |
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